


Holsom Prison Blues

by theladymondegreen



Series: Kink Bingo 2019 [3]
Category: Check Please! (Webcomic)
Genre: (does that even make sense?), Accidental Voyeurism, Friends to Lovers, M/M, Masturbation, Oral Sex, Prison, elements of exhibitionism, it takes prison to make these boys talk about their feelings, they're in a prison there isn't much privacy
Language: English
Status: Completed
Published: 2019-01-30
Updated: 2019-01-30
Packaged: 2019-10-19 14:22:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,476
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17602985
Author URL: https://archiveofourown.org/users/theladymondegreen/pseuds/theladymondegreen
Summary: There's a saying: "A friend will bail you out of jail, a best friend will be in jail with you." Ransom and Holster are best friends.Alternatively: Prison forces Holster and Ransom to actually discuss their feelings.





	Holsom Prison Blues

**Author's Note:**

> Written for the “Location: Prison Cell” square on my kink bingo card. Title is inspired by the Johnny Cash song “Folsom Prison Blues”.

“So they still haven’t agreed to release either of you on bail,” Shitty said, “You’re too much of a ‘flight risk.’” He actually made the air quotes as he said it. “I’m gonna keep trying, but it’s looking like you two are going to be in here until the trial. At which point you won’t be here, because we’re gonna win. The team’s got a strong case already, and we’re not above using technicalities to get you out.” He ran his hand through his hair, pushing it back from his face, “Unfortunately, it’s looking like those technicalities are our only chance. How did you guys manage to get someone so angry with you that they’d frame you for arson?”

“Fuck the LAX bros,” Ransom and Holster said in unison, weaker than the normal shout.

Shitty nodded sagely, “That’ll do it. I’ll remind the PI to look into them.”

Shitty left them and the guard escorted them right back to the room they fortunately shared. The cell was smaller than the attic they had shared, and made of cold cinder block, but the bunk beds in the corner made it feel like some echo of the attic in the Haus. Admittedly, not one they’d choose, but familiar none-the-less.

Holster flopped on the bottom bunk as the cell door slammed closed, “Two more months of this.”

Ransom flopped down beside him, “At least.”

“Bro.” Holster rolled onto his side to face Ransom, “Shitty’s the best lawyer we know, he’ll get us out.”

“And then they’ll deport me because I have a criminal record.”

Holster grabbed Ransom’s hand, “You know that’s not how it works. He’ll get the charges dismissed for sure. And if he somehow doesn’t, I’ll sneak into Canada.”

Ransom laughed weakly, “Maybe don’t plan future crimes quite so loudly, I’m pretty sure everyone in the cell block heard that.” He squeezed Holster’s hand. “I’m glad I’m in here with you.”

Holster squeezed back.

* * *

One more month to the trial. Ransom laid on the top bunk, studiously trying to ignore the shaking of the bed frame and the sound of Holster’s hand sliding up and down. A gasp, just loud enough to hear, had him swelling in his pants. The next bitten off moan had him reaching down, timing his strokes unconsciously with the shaking of the bed.

* * *

Three weeks to the trial. Holster had jerked off every night for the last week, and that night was no exception. Ransom was more than primed at that point, and had started at the same time Holster did. One particularly vicious tug, catching his head just right, had him out-and-out whimper.

The sounds below him stopped, and Ransom swore so did his heart.

“Ransom?” Holster’s voice broke the quiet.

“Yeah?” he said, trying and failing to sound normal.

“You know I can always tell, right?” Holster said quietly.

Ransom’s erection abruptly wilted.

Holster continued, “I don’t mind.” (He didn’t exactly sound sure of himself.) “It’s boring and it’s not like we’ve got hook-ups in here.” He paused and audibly swallowed. “And, if I’m honest with myself…” Pause again, “If I’m honest, there’s only one person I’ve been interested in for a while…”

Ransom had no idea why his heart felt so heavy at that. “I’m not following,” he said, as much as he wished this conversation could just be over. Holster obviously felt the need to say something, and he wasn’t going to stop his best friend from getting something off his chest if he could help it.

Holster sighed, “God, Justin, you’re supposed to be smart.”

“Weak chirp,” Ransom fired back, “Keep going.”

Another long pause, this one enough to get Ransom to roll over and peek down into the bottom bunk. “You okay?”

It was hard to tell in the dim lighting leaking in from the hallway, but Holster’s face was awful red.

He sucked in a big breath, “Ransom- Justin, what I’m trying to say is I think I’m in love with you. Have been for a while. And I’m sorry if it makes it weird but I couldn’t just lie to you anymore and pretend I’m not super into listening in while you jerk off.” He hadn’t paused for a breath in that whole thing, and as soon as he was done he rolled over, facing the wall.

Ransom slid off the top bunk, sitting down next to Holster and resting a hand on his shoulder. “We really have to work on your volume control. Half the prison probably heard that. But I’ve got something for just you to hear.” He leaned in and whispered, “I think I’m in love with you, too.”

Holster turned to face him so violently that he nearly fell right off the bed. “What?”

“Bro, you weren’t the only one who liked listening in. And we’ve been bros for years. You’re the most important person to me by far.”

“Really?”

“I was serious when I said I was glad I was here with you. If I had to be stuck in prison with anyone, I’d pick you.”

Holster was a bit teary-eyed when he grabbed Ransom in a hug around the waist. Ransom was abruptly reminded that he hadn’t gotten off yet when he felt Holster’s face right up against the now-interested party.

“Uh.” He said eloquently.

Holster stiffened as he realized what was happening inches from his face. Then he relaxed and shuffled closer, his cheek resting directly on what was becoming an urgent problem for Ransom, separated only by the material of his pants. “We could get back to what we were doing,” Holster said.

Ransom let out a dismayed sound at the thought of separating and losing the delicious pressure on his dick.

“Or,” Holster said, sounding distinctly pleased with himself, “We could do something better.”

Ransom could only nod. Holster took the opportunity to slide his pants down enough to free his erection. He licked his lips, then he frowned, “Shit, no condoms.”

“Shit.” The disappointment wasn’t enough to even take the edge off the desire Ransom felt, “Hand jobs?” he offered.

“But I really wanted to suck your dick,” Holster whined, “It’s right there.” His face was still inches away. “I’m clean,” he said abruptly, “Haven’t done anything risky since I was last tested.”

Ransom’s heart wasn’t going to be able to handle the rapid up and downswings of the night, “Me too,” he said, “Unless you count trying to get a blow job in prison, which might be the definition of risky.”

Holster took that opportunity to pounce, immediately surrounding the head of Ransom’s dick in wet heat. He tongued around the tip and Ransom had to clutch at his hair.

“Shit,” he said weakly. Holster responded by humming and sliding further down, until he nearly gagged. Ransom thought it was just about the best thing until Holster slipped a hand around to fondle his balls. He couldn’t stop himself from bucking his hips.

Holster immediately pulled off, coughing, “Let’s save the deep throating for later?”

“Sorry.” Ransom couldn’t even find it in himself to feel embarrassed, he was feeling that good. Especially while Holster was still playing with his balls. Holster took the pause as an opportunity to reposition himself, sliding off the edge of the bed to kneel between Ransom’s legs. One hand returned to his balls while the other grasped the base of his dick. Ransom tensed with the desire to thrust when Holster ducked back down to suck him back in.

Holster pulled back off and Ransom nearly whined with disappointment, “You don’t have to hold yourself so still,” he said, “That’s what this is for.” He squeezed Ransom lightly with the hand wrapped around the base of his dick, then soothing it with a stroke to the tip and back, “You won’t be able to thrust too deep this way.”

He couldn’t keep from minutely moving his hips after those instructions, especially when Holster backed off to just the tip, tonguing at his slit for a moment before sliding back down.

“I’m close,” he warned.

Holster just hummed and kept going. The hand on his balls disappeared, and seeing Holster reach into his pants to jack himself off was enough to send him right over the edge, coming in Holster’s mouth. Holster kept working his cock until he was finished.

He sagged back against the wall beside the bed, catching his breath. “I’ll get you in a minute,” he said.

Holster grunted, clutching at Ransom’s leg with his free hand as he came. “Get me next time,” he grinned, “I got this one handled.”

Ransom’s dick made a valiant attempt at hardening again.

“Woo! Get some!” someone shouted from a cell near theirs.

And all trace of hardness was gone. “Next time isn’t until after we’re out of here,” he hissed.

He was wrong. They didn’t last two days.

**Author's Note:**

> This one was a bit of a struggle. The first draft was weird and barely filled the prompt, plus I kept stalling out on it. This version was written in one sitting and actually did the prompt justice.


End file.
